(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

Base Information

Chemical Name:(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one
CAS No.:360558-65-2
Molecular Formula:C₂₄H₂₇BrFNO₃
Molecular Weight:476.386
Hs Code.:

Synonyms:(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

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Chemical Property of (2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

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Technology Process of (2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

There total 12 articles about (2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (R)-2-Fluoro-3-nitromethyl-4-phenyl-butyric acid

: 360558-65-2
(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: (COCl)2; DMF / CH₂Cl₂ / 0 - 23 °C

2.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C

3.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

4.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

5.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

6.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

6.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

6.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

7.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C

8.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C

With lithium borohydride; oxalyl dichloride; methanesulfonic acid; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja010113y

Reference yield:

: (R)-2-Fluoro-3-nitromethyl-4-phenyl-butyryl chloride

: 360558-65-2
(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

3.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

4.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

5.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

5.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

5.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

6.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C

7.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C

With lithium borohydride; methanesulfonic acid; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; hexane; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja010113y

Reference yield:

: 360558-58-3
(R)-1-Diazo-3-fluoro-4-nitromethyl-5-phenyl-pentan-2-one

: 360558-65-2
(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

2.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

3.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

4.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

4.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

4.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

5.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C

6.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C

With lithium borohydride; methanesulfonic acid; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja010113y